Fri Mar 29, 2013 at 10:07:53 AM EDT

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The contest to succeed the retiring John DeStefano as mayor of Connecticut's second largest city is shaping up as a battle between "establishment" candidates with ties to traditional power centers in the city and outsider figures who have built their own political support bases as reform-minded, activist legislators at the local and state level. In part the difference between the insider candidates (Probate Judge Jack Keyes and former economic development czar Henry Fernandez) and the outsider candidates (State Representative Gary Holder-Winfield and Alderman Justin Elicker) is defined by age: the two outsiders are both under 40, approximately the age that DeStefano was when he took the helm in 1994; while Judge Keyes, with close ties to Martin Looney and elements of the old Democratic Party machine, is in his sixties. (He served several terms as City Clerk when Elicker and Holder-Winfield were still in diapers.) Henry Fernandez is only 44, but he is the candidate most closely associated with the old guard around DeStefano, and most likely to pick up support from the business establishment and other institutional interests that have traditionally bankrolled DeStefano's campaigns.

The outsiders suffer from the fact, or at least the perception, that they are inexperienced two-term legislators without deep ties to New Haven, both having moved to the city since 2000. Neither has citywide name recognition or an obvious base of support. Elicker is popular in a largely minority area (Cedar Hill) that he has represented since 2010, and in the most recent municipal redistricting he inherited a heavily Latino area in Fair Haven. But conventional wisdom is that he will struggle in the Latino and African-American communities, which make up more than 50% of the city's population, without support from clergy, organized labor or other traditional power-brokers. Holder-Winfield's problem is that he is more popular in progressive activist circles around the state, and better known in the corridors of the state capitol, than he is in New Haven. Many in the African-American community believe he has not 'paid his dues' and would prefer a different black candidate, such as Kermit Carolina, principal of one of the city's largest high schools.

The other fault-line separating the insider and outsider candidates is public financing. New Haven is the only city in the state with a public financing system for municipal elections. Established in 2006, the New Haven Democracy Fund provides both grant and matching funds to participating candidates, while limiting the size of individual contributions to $370 and limiting overall campaign spending. The outsider candidates have been unequivocal in their support for the Democracy Fund; on Thursday Holder-Winfield held a press conference on the steps of City Hall to criticize candidates eschewing the Democracy Fund, and a resolution has been introduced at the Board of Aldermen by an Elicker ally that would call on all mayoral candidates to participate in the clean elections program. Meanwhile, the insider candidates have made lame and unconvincing excuses for not participating, aware that their success may hinge on raising large checks from institutional interests.

Interestingly, after criticizing the Democracy Fund in recent years and declining to participate when he ran for his record-breaking tenth term in 2011, Mayor DeStefano has included $200,000 in his proposed 2013-2014 budget to replenish the fund, suggesting that (like Jodi Rell with the state Citizens Election Program) he recognizes that it is important to his legacy. (Read more about that here: http://newhavenpolitics.tumblr... ) Philosophically most Democrats believe in campaign finance reform and clean elections; but sometimes they are willing to suspend those beliefs for reasons of political expediency. Despite abandoning the Democracy Fund in 2011, DeStefano still won by double-digits. Will New Haven Democratic primary voters in 2013 be equally indifferent to a blatant display of 'situational ethics?'

Finally, racial politics cannot be ignored. Race is an issue in the mayoral contest but only indirectly. The insider/outsider fault-line transcends race: Elicker is white, and Holder-Winfield is black; Keyes is white and Fernandez is Latino. But it is undeniable that Fernandez's background will help him sew up Latino support; that Keyes and Elicker, though representing different elements of the Democratic Party, could end up fracturing the vote in the wealthier and whiter neighborhoods, benefiting the minority candidates; and that a second viable black candidate like Kermit Carolina would seriously compromise Holder-Winfield's ability to win.

Who becomes mayor in 2014 will depend largely on which side can more successfully tarnish its opponents: can the establishment candidates successfully portray the outsiders as inexperienced carpetbaggers, or will the outsiders succeed in depicting the establishment figures as too closely tied to John DeStefano and other power centers that have become irrelevant or discredited? Stay tuned for an exciting conclusion to the New Haven Mayoral Showdown of 2013!